


Let's Talk About Sex!

by KuriKuri



Category: Teen Wolf (TV)
Genre: Alternate Universe - College/University, Alternate Universe - No Werewolves, Blow Jobs, Loss of Virginity, M/M, Safer Sex, Sex Education, Virgin Derek
Language: English
Status: Completed
Published: 2014-10-08
Updated: 2014-10-08
Packaged: 2018-02-20 10:09:22
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,241
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2424863
Author URL: https://archiveofourown.org/users/KuriKuri/pseuds/KuriKuri
Summary: <blockquote class="userstuff">
              <p>“Hey, you doing okay?” Stiles questions, a concerned look on his face, and Derek realizes that he hasn’t replied. “You know, this is just the sexual health clinic. The actual clinic is over – ”</p><p>“Dental dams,” he blurts out, cheeks heating as he continues to stare at Stiles. “I, uh, need dental dams.”</p><p>(Or: In which Stiles works at the Student Sexual Health Center and Derek uses sex questions as an excuse to talk to him.)</p>
            </blockquote>





	Let's Talk About Sex!

**Author's Note:**

> Inspired by [this](http://bleep0bleep.tumblr.com/post/97619273895/hi-carrie-in-the-sterek-headcanons-of-your-heart-do) headcanon post by bleep0bleep. 
> 
> Trigger Warnings: None

To say that Derek is embarrassed is so much of an understatement he might as well be in Australia right now. He has no clue how it happened, how Laura had managed to bully him into going to the student health center to pick up _dental dams_ for her and her girlfriend, Braeden. He thinks she said it had something to do with trying to get him laid. Not that he actually cares about getting laid –

Okay, so maybe he does a little bit.

Because the guy sitting next to the overfilled basket of condoms is hot like burning, and also happens to be the guy Derek spent all last semester daydreaming about in their Modern Asian Literature class. Derek’s pretty sure his name is Stiles, because he may or may not have stolen the class roster. Only temporarily, though. Really, ‘borrowed’ is the more appropriate term.

“Need any help there, big guy?” Stiles asks, an amused smile on his face as he looks up at Derek through his eyelashes.

Fuck, those eyelashes are to die for.

“Hey, you doing okay?” Stiles questions, a concerned look on his face, and Derek realizes that he hasn’t replied. “You know, this is just the sexual health clinic. The actual clinic is over – ”

“Dental dams,” he blurts out, cheeks heating as he continues to stare at Stiles. “I, uh, need dental dams.”

“Oh, okay. Cool,” Stiles replies, smiling again, but for some strange reason Derek can’t help but think that it looks a little more forced than before. “I think we still have some.”

“Thanks,” Derek mumbles, face still burning as Stiles ducks down to check one of the desk drawers.

“Hey, but for future reference, though, you can always convert a condom into a dental dam,” Stiles says, popping back up with three brightly colored packages in his hand. “Just cut off the tip and then cut it down the side so you have a rectangle and voila.”

And wow, now Derek’s imagining Stiles going down on some lucky girl and he can’t tell if he’s more turned on or jealous. Is that even a thing? Jealous but horny?

“You know, it’s really awesome that you’re doing this, dude,” Stiles continues, breaking Derek out of his daze. He hopes he’s not breathing heavily or drooling. Fuck. “I mean, there are so many douches out there who get so squeamish about giving head, it’s just ridiculous. It’s even better that you volunteered to get the dental dams instead of making your girlfriend do it. Safe sex is sexy, dude – _own_ it.”

Derek wonders if Stiles would find it sexy if he ripped a condom open right now. With his _teeth_.

“Derek,” Derek blurts out, because apparently his brain is having a difficult time functioning today. Then again, maybe it has to do with his proximity to Stiles. He’s pretty sure the reason he got a B- in Modern Asian Lit is because he kept getting distracted by Stiles.

“Derek?” Stiles repeats, clearly confused.

“Derek,” he replies, by way of explanation. “Not ‘dude.’” 

“Oh, got’cha,” Stiles says, smiling that stupidly sexy, lopsided grin of his. “I’m Stiles.”

Somehow Derek just barely manages to refrain from saying, _I know_. Because that would be weird. And creepy. (Although he’s been reliably informed by his sisters that he has a natural creeper tendency.)

“Thanks,” Derek replies awkwardly, unsure what else to say. “For the dental dams.”

“Anytime, Derek, anytime,” Stiles laughs, and Derek’s more than a little distracted by his pink, cupid’s-bow mouth. “Now go forth and have mind-blowing sex.”

Again, Derek tries to avoid thinking about sex with Stiles and whose mind he’s rather be blowing. It wouldn’t even have to be Stiles’ _mind_ he’s blowing. Really, he’s not picky.

“Do you have any other questions? Or, uh…?” Stiles asks tentatively, and Derek abruptly realizes that he’s just standing there, staring at Stiles while holding multiple brightly colored dental dam packets. “Seriously, I can probably answer anything.”

Wow, Stiles really isn’t making it easy for Derek to stop thinking about sex. Then again, he supposes they are in the Student Sexual Health Center.

“I’m fine. I’ll just – ” He motions over his shoulder towards the door. “ – leave now. Thanks for the – ” He stutters again, cheeks turning pink. “ – stuff.”

He flees. It really isn’t his proudest moment.

\---

Derek Hale is, once again, standing right outside the front doors of the Student Sexual Health Center. He’s debating whether to go in or not. Really, this is a new low for him, being desperate enough to talk to Stiles that he’d willingly make up random questions about sex (which he really doesn’t care about the answers to) just to have an excuse to see him.

“Hey, Dental Dam Derek, right?” a voice says from somewhere behind him, nearly startling him out of his skin. “Or do you prefer just Derek?”

He turns around to find the source of the talking and, as he suspected, it’s Stiles. He can already feel his cheeks flushing as the nickname catches up to him, but he can’t quite find the words to respond with at the moment. They’d probably just come out in a jumbled mess.

“Wait, are you leaving right now?” Stiles continues on, looking strangely disappointed. “Don’t tell me you’re cheating on me with Erica. I thought we had a real connection last time.”

“Uh,” Derek replies intelligently, cheeks flushing impossibly redder from Stiles’ teasing as he glances back at the still closed door of the health center “I just got here.”

“Oh, cool,” Stiles says, grinning again. “Well, come on in. What is it this time? More dental dams?”

“Questions, actually,” Derek answers, trailing after Stiles awkwardly and trying to ignore the way the blonde woman currently at the desk narrows her eyes at him before giving him a knowing smirk. She looks vaguely familiar and he thinks he might have had her in his chemistry discussion freshman year.

“Hey, Erica,” Stiles greets her, setting his backpack down next to the desk while she begins to pack up her own stuff.

“Stiles,” she replies, eyes darting between him and Derek. “This wouldn’t happen to be Dental Dam Derek, would it?”

“Is that what _everyone’s_ calling me?” Derek grouses, and he can feel his cheeks flushing again. “I only came by for them once.”

“Yeah, well, not a lot of people come here for dental dams,” Stiles says, shrugging and sitting down in Erica’s now vacated seat. “Mainly I just hand out condoms and check people in for their appointments.”

“Oh,” Derek replies, for a lack of anything better to say.

“I’ll leave you two to it, then,” Erica butts in, leaning over to press a light kiss to Stiles’ forehead before giving the two of them a wink and sauntering on out.

“Your girlfriend seems… nice,” Derek says once the door’s closed behind her, trying not to feel too jealous and mostly failing, because _of course_ Stiles is already taken.

“Girlfriend?” Stiles asks, blinking at him for a moment in confusion. “What, Erica?”

Derek shuffles his feet and nods his head awkwardly.

“Uh, no. I’m pretty sure Boyd would kill me if I ever tried anything,” Stiles snorts, leaning back in his chair and tilting his head a little in order to look up at Derek. “Not that I’m interested.”

It almost seems like Stiles adds on the ‘not that I’m interested’ part a little too quickly, but Derek can’t for the life of him think of why he’d do that. Well, he supposes that maybe Stiles would do it if he was interested in Derek, but clearly that’s not the case if he can’t even remember that they had a class together last semester. It wasn’t even a big class – only about twenty students!

“Anyway, questions!” Stiles continues, and maybe it’s just Derek’s imagination, but it almost looks like he’s blushing slightly.

“Anal sex,” Derek blurts out, the words just kind of tumbling out of his mouth.

“Giving or receiving?” Stiles asks, taking Derek’s awkwardness in stride, a small, amused smile on his face now.

“Uh, both,” Derek answers, barely resisting the urge to fidget.

“Good answer,” Stiles replies, his small smile turning into a full-fledged grin and Derek’s already starting to regret his idea to ask Stiles sex questions as a way to see him more often. Maybe he can subtly acquire Stiles’ schedule and try to transfer into one of his classes. You know, even though the add/drop deadline has long since passed. Fuck.

“So,” Stiles continues, breaking Derek out of his momentary daze again. “Are we talking just girls here, or…?”

“I said both giving and receiving,” Derek replies, frowning a little. He’d been trying to subtly hint to Stiles that he was bisexual, but had he somehow been too subtle?

“Hey, man, don’t knock strap-ons until you’ve tried them,” Stiles says, raising an eyebrow at Derek who blinks at him blankly for a moment before turning red again, trying not to think about Stiles getting fucked like that, face pressed into a pillow and ass high in the air with a gorgeous woman behind him. “I mean, the real thing is great too, but Lydia Martin is a _beast_ with one, let me just say.”

Derek has no clue who Lydia Martin is, but it seems like being simultaneously turned on and jealous is going to be his default reaction to Stiles nowadays.

“I’m bisexual,” Derek finally admits, still looming awkwardly above Stiles, who has to tilt his head back a little to make eye contact with him. It does give him a good view of Stiles’ mole dotted neck, though.

“You can pull up a chair, you know,” Stiles says, leaning over the desk a little and propping his chin up on his hand. “And I’m bisexual, too, so I’m not gonna, like, judge you or anything.”

“I didn’t think you would,” Derek replies, because, honestly, it had never even occurred to him. Which, yeah, was probably kind of naïve of him, but still. Despite how awkward he is around Stiles – especially when talking about sex – something about Stiles makes him feel comfortable.

Of course, finally pulling over a chair and sitting down only serves to make him more comfortable.

“So, where were we?” Stiles muses, worrying his lower lip distractingly. “Giving and receiving anal sex for both men and women, right?”

“Right,” Derek mumbles, face turning red again.

“Okay, I guess I’ll start with guys first, because I’m more familiar with that, being, you know, a guy,” Stiles says, a little lopsided smile on his face and a spark of something Derek can’t quite identify in his eyes. “First off: lube. Always use it, unless you’re having sex, like, three times a day and are loose enough. And when I say lube, I mean _actual_ lube, preferably water-based, because you can get infections from other stuff like lotion. I mean, lotion tends to be okay if you’re masturbating and not trying any anal play, but otherwise keep it away from your ass or anyone’s vagina.”

Yeah, Derek really doesn’t think he’s going to be having sex of any sort three times a day, considering he hasn’t even had sex _once_. Ever. In his life. Idly, Derek wonders if Stiles is the sort of person who likes to go all day, which really isn’t the sort of thing he should think about when Stiles is _sitting right across the desk from him_.

“Hey, can you give me your hand for a sec?” Stiles asks, and Derek frowns at him, a little confused, but holds out his right hand anyway.

Taking it in his own hands, Stiles fixes his eyes on it intently and examines Derek’s fingers carefully, and Derek has to resist the urge to shiver as Stiles’ hands brush against his own. He has absolutely no clue what Stiles is trying to do, but he’s certainly not going to complain. He also wouldn’t be opposed to Stiles sucking on his fingers just a bit. For reasons.

“You have nice fingers,” Stiles says idly, and maybe Derek’s imagining things again, but he could almost swear that Stiles’ pupils dilate slightly. “They’re pretty large, so unless you or your partner is really big, you’ll probably only need to use two to stretch you or them out. If you’re really worried, though, three’s a good idea. I’d suggest practicing on yourself first before trying it with anyone else, though.”

And okay, so maybe Derek’s never actually had sex before, but he’s no stranger to using his fingers to get himself off. Not that Stiles needs to know that if it means he’s going to spend longer touching Derek’s hands like this.

“You, ah, know a lot about that?” Derek asks, immediately wincing at the words leave his mouth. Hopefully Stiles wont’ freak out too much about Derek trying to hit on him when he’s been so patient and helpful already.

“Long fingers have their advantages,” Stiles replies, that heated glint in his eyes again and a smirk on his face, “and I’m not just talking about piano playing.”

Clearly Stiles is trying to kill him with sexiness. He’s getting _very_ close to succeeding.

“Anyway, so, moving on. If it’s your first time or their first time, do the prep really thoroughly. Use way more lube than you think you’d ever possibly need. Trust me, you don’t want to mess this up,” Stiles says, grimacing slightly, Derek wincing in sympathy. Not that he would actually know, of course. “As for the prostate, have you ever, uh, tried finding yours before?”

“A couple of times,” Derek mutters, blushing brightly.

“You know what it feels like, then,” Stiles continues, wetting his lower lip with his tongue distractingly. “It’s a bit harder to find on someone else, and it won’t always be obvious right away when you find it, so talk to your partner throughout. Shallow thrusts tend to work best for prostate simulation when you move on from fingers, but don’t knock hard and deep either.”

Nope. He’s really not thinking about fucking Stiles hard and deep right now. Not at all. Shit.

“As for girls, prep’s the same. Never go between vaginal and anal without changing the condom or washing your dick or both,” Sties goes on, completely oblivious to the internal crisis Derek’s having. “Anal tends to be less pleasurable for them, but if you do it right, you can simulate their vagina and g-spot, too.”

Derek pretty much missed all of what Stiles just said, but honestly he’s not all that disappointed. Truth be told, he doesn’t really care about the answers to any of the questions he’s asking – he just wants an excuse to sit and stare at Stiles for a while. Which, granted, is kind of creepy.

“Uh, yeah. I think that’s about it for Anal Sex 101,” Stiles finishes, breaking Derek out of his daze, still looking over at Derek from under those long, gorgeous eyelashes of his.

“Thanks,” Derek says, his voice more than a little gruff, and he really hopes that Stiles just attributes it to him being grumpy or something.

“Hey, like I said, I’m here to help,” Stiles replies, smiling that lopsided grin of his. “Now go get ‘em, tiger. I expect to see you in my Anal 201 class soon.”

Stiles winks. He fucking _winks_. Derek’s _so_ fucked, and not even in the sexy way.

\---

It’s been two days and Derek hasn’t been back yet. _Yet_ , because, god, these past few days have been torture. It feels like everywhere he turns he sees Stiles, only to realize that it’s just someone with a slightly similar figure or hair color or voice. He feels guilty, holed up in the apartment he shares with his sister, jacking off to the memory of Stiles’ hands on his.

On the third day, he breaks down.

“So, how’d it go?” Stiles asks as soon as he enters the Student Sexual Health Center, beaming brightly at him.

Derek grunts noncommittally as he pulls up a chair next to the desk again, and Stiles’ face falls, making Derek regret his answer immediately. What’s he supposed to say, though? That he didn’t actually have sex with anyone, because he was just asking as an excuse to talk to Stiles?

“It was good,” Derek corrects himself quickly, before Stiles can say anything. “I just don’t kiss and tell.”

“Oh, sorry, dude,” Stiles replies, and for a moment Derek thinks he hears Stiles mutter, “Oh my god, you’re so fucking cute,” under his breath, but that’s probably just his imagination.

“I have some more questions for you, though,” Derek continues, willing himself not to blush as Stiles’ eyes light up again.

“Shoot,” Stiles says, smirking.

\---

When Derek gets home that night, he scours the internet for porn and makes a list of questions to ask Stiles. It should get him through the next three months if he goes every other day.

Fuck, he’s desperate.

\---

“Blowjobs?” Derek asks, trying not to stare at the way Stiles is sucking on the end of his pencil.

“Male, I’m guessing, Dental Dam Derek?” Stiles replies, grinning and waggling his eyebrows.

\---

“Flavored lube,” Derek says without hesitation, not really phrasing it as a question.

“System Jo’s Cherry Burst is the _best_ ,” Stiles answers in a way that’s a little too close to a groan for Derek’s sanity. “Seriously, I want a job as a tester for them.”

\---

“Bondage…?” Derek asks a little nervously, adjusting his glasses, even though he’s gotten much more comfortable with asking Stiles sex questions recently.

“Start with bondage tape – there’s a lower chance of you cutting off your circulation. If you like that, you can graduate to things like cuffs. I prefer leather,” Stiles answers evenly as Derek tries not to let his eyes glaze over at the thought of leather handcuffs biting into the soft skin of Stiles’ wrists. “I think the campus Office of LGBTQ Affairs has an informal class. Just let me find the pamphlet…”

\---

“Ever had a threesome?” Derek asks, trying for casual, but willing to risk phrasing the question in more of a personal manner this time. He brought coffee, after all.

“Nah,” Stiles answers after taking a sip, surprising Derek. “I almost did, but when I introduced the other two, they seemed a little too into each other, so I backed out. They sent me a wedding invitation last week.”

\---

“Lingerie?” Derek questions, settling back in the chair he’s come to think of as his.

“If it’s for someone with lady parts, talk to Lydia,” Stiles says, gratefully accepting the coffee cup Derek hands him. “If you want some for yourself, I can write down some websites for you.”

\---

“Do you prefer to top or bottom?” Derek asks, trying to be nonchalant about it and not show how personally invested in this question he is.

“I like both,” Stiles replies, tapping his coffee cup against his lower lip. “Maybe bottoming, though? I kind of like it when my partner gets a little rough with me.”

\---

Derek’s pretty fed up with today. As in, the _entire_ day, because it’d started with little things like Laura and Braeden using up all the hot water in the apartment, but now it’s escalated to huge things like his Latin American History professor _losing_ his fucking essay and trying to claim that he’d never received it in the first place.

He doesn’t even realize he’s automatically gone to the Student Sexual Health Center – to _Stiles_ – until he walks through the doors and sees Stiles sitting at his desk like always, messing around on his phone with his feet propped up on another chair.

“Heya, Derek,” Stiles greets him, grinning lazily, eyes bright, although his smile rapidly decreases as he takes in Derek’s expression. “Damn, what happened? You look like shit.”

“Thanks, Stiles,” Derek grouses, his tone sarcastic as he drops himself down into a chair heavily. “That’s exactly what I wanted to hear.”

“Seriously, big guy, what’s up?” Stiles asks, his tone a little softer now as he sets his phone off to the side and even turns it off. For some reason the little gesture makes butterflies flutter around Derek’s stomach.

“My _idiot_ professor lost my essay,” Derek sighs, knowing that he shouldn’t be taking his frustrations out on Stiles. “Instead of owning up to it, though, he fucking accused me of never turning it in in the first place.”

“Shit, that sucks,” Stiles says, a sympathetic expression on his face. “Who’s the prof?”

“Daniels,” Derek replies, scowling at the mere mention of the name. “Post WWII Latin American History.”

“You’re a history major?” Stiles asks, and Derek abruptly realizes that, for all the talking they’ve done, he knows Stiles’ favorite flavor of lube but not his major.

“Yeah,” Derek answers after a moment – when he realizes he’s supposed to answer. “You?”

“Criminology,” Stiles replies evenly.

“Not something health related?” Derek asks, a little surprised, because that would certainly make more sense with Stiles working in the health center.

“Nah. This is just a hobby,” Stiles answers, a hint of a smile appearing on his face again. “I figured I might as well put my sexual experience to use.”

Derek just barely resists the urge to point out another way in which Stiles could use that experience. One that might also involve Derek, and possibly a bed. A couch or the wall works, too – he’s not that picky.

“Was Modern Asian Lit to fill a requirement, then?” Derek asks before he can censor himself. Fuck, Stiles is going to have him figured out in _minutes_.

“You remember that?” Stiles replies, blinking in surprise.

“Of course I remember that class. It kicked my ass,” Derek snorts, deftly avoiding the question at hand. Or, well, as deftly as possible.

“No, I mean – ” Stiles stutters, blushing slightly, and now _Derek’s_ the surprised one. “You, uh, remember that I was in it?”

“There weren’t exactly a lot of us,” Derek says, shrugging and trying to ignore the way his palms are sweating. “Why, do you remember me?”

“Yeah,” Stiles mumbles, still blushing, and wow, this is the most embarrassed Derek’s ever seen him and they’ve had in-depth conversations about the best positions for gay sex. “I just, you know, didn’t want to make things awkward when you first came in, considering you were asking for dental dams and all.”

“It wouldn’t have made things awkward,” Derek says, and really, it probably would have made him more confident.

“Well, I wasn’t sure if you’d recognized me anyway,” Stiles replies, shrugging and not quite meeting Derek’s eyes. “I mean, I didn’t really participate much, because I spent most of the class mooning over this super hot guy, so…”

“Oh,” Derek says, trying not to feel too crushed by the fact that Stiles spent the entire semester they shared a class pining after someone else.

“Anyway, enough of that,” Stiles announces when Derek doesn’t say anything else, finally meeting his eyes again. “What’s your question for today?”

“I – ” Derek starts, cutting himself off abruptly as he realizes that he’s come to the end of his list. “I don’t have one.”

“Oh,” and it’s Stiles’ turn to say it this time as a distinct air of awkwardness settles over them.

“I can go, if – ” Derek says, already grabbing his backpack.

“No!” Stiles blurts out, stopping Derek in his tracks, making him look over again to find Stiles still blushing, although Derek has no clue why. “No, you can, uh, stay. If you want. I mean, I’m not going to hold you hostage or something – ”

“I don’t know, it seems like you have more than enough bondage gear for it,” Derek shoots back dryly, but he relaxes and settles back down in his chair.

“Hey, _consent_ ,” Stiles replies, his tone chastising. “I only tie down people who want to be tied down.”

Derek just barely resists the urge to tell Stiles that he can keep him tied down forever, and not necessarily in the literal sense.

\---

It’s been nearly two weeks since he and Stiles started talking about things other than sex and Derek’s on cloud nine. Seriously, the only way his life could get better would be if Stiles asked him out on a date. The likelihood of that is about nil, though, so Derek’s willing to be happy with what he can get.

“Hey Derek,” Laura says from where she’s sprawled out on the couch when he gets back to the apartment, fresh from another chat with Stiles.

He makes a noncommittal noise, but doesn’t otherwise acknowledge her greeting, already heading to his room.

“So I went by the library today,” she continues, raising her voice a little as he passes, her words making him stop in his tracks. “Funny thing was, I didn’t see you there.”

Oh, yeah. That. He may or may not have told his sister that he’d been hanging out with a study group at the library, preferring lying to admitting to her that he was going to the Student Sexual Health Center to ask a cute guy sex questions.

“Laura – ” he groans, shooting her a pleading look, hoping she won’t press for answers. Of course, it’s _Laura_ so of course she’s going to need to know.

“Nuh uh,” she says, shaking her head. “You’re not getting out of this one, Der. I would think you’re off finally getting laid, but I have yet to see any hickies.” 

“I could be good at hiding them,” Derek protests, mildly affronted.

“Anyone who’s had a hickey in an inconvenient spot before knows that they’re a _bitch_ to cover, even if you do have experience with makeup,” Laura snorts, clearly not buying his protests.

“Shut up,” Derek grouses, jaw tense. “I was just hanging out with a friend. There’s nothing else going on.”

“Which is why you were sneaking around and lying about it,” Laura says, shooting him an unimpressed look.

“Look, I had a crush on him a while ago, okay?” Derek sighs, finally giving in to his sister, at least to a certain extent. “But now we’re friends, and I didn’t want you to make things weird by trying to set us up.”

“When have I ever done that?” Laura huffs, indignant, crossing her arms over her chest.

“Seventh grade, freshman year, junior year, senior year, freshman year again – ” Derek lists off, rolling his eyes and holding up fingers.

“Fine, okay! I get it,” she exclaims, scowling at him, cheeks a little pink. “I won’t try to set you up with your mysterious friend.”

Derek lets out a sigh of relief.

“That doesn’t mean I’m going to stop trying to set you up with other people though,” she continues, her voice almost cheery and a smirk on her face.

Derek scowls at her and marches off to his room, slamming the door behind him.

\---

“You look like shit,” Derek announces as he sits down across from Stiles in his customary spot, sliding a cup of coffee towards him.

“What was it you said to me when I told you that?” Stiles huffs, narrowing his eyes at Derek, but he accepts the coffee anyways. “Something along the lines of, ‘thanks, Stiles, that’s _exactly_ what I wanted to hear.’”

It’s true, though – Stiles _does_ look like shit. He has the beginnings of dark circles under his eyes and a tired expression on his face. Normally his hair’s sticking up at all different, impossible angles, but today it looks limp and – well, Derek would say ‘downtrodden’ if it was possible for hair to be downtrodden. It’s still messy, of course, but it’s a sad sort of messy, not his typical sex hair sort.

“So, are you going to tell me what’s wrong, or am I going to have to pry it out of you?” Derek asks, still studying Stiles’ expression carefully.

“I just – I’m trying to convince a friend to go on birth control,” Stiles sighs after a moment, clutching his coffee cup tightly. “I mean, she has severe periods – like, she bleeds twice as much as she should and her period lasts for three or so days longer than average and stuff. Her doctor already wants to prescribe her hormonal pills to regulate it, but she keeps refusing.” 

“Why?” Derek asks, confused, a frown twisting his lips.

“She doesn’t have a boyfriend and she’s worried about people thinking she’s a slut or something,” Stiles answers, a disgruntled look on his face. “Also, her parents are worried that it’ll encourage her to have unsafe sex, which is _completely_ ridiculous, because she’s twenty years old and her parents should _not_ be dictating her sex life. Also, it’s a fucking _medical condition!_ At this rate she’s going to become anemic.”

“I’m sorry,” Derek replies after a beat of silence, because what else is he supposed to say to that?

“It’s not like it’s your fault,” Stiles says, waving away his concerns. “Like, I just wish that society wasn’t so obsessed with this whole virgin-slut dichotomy, you know?”

“Yeah,” Derek echoes, cheeks flushing slightly, the word ‘virgin’ ringing in his ears.

“I mean, when I was in high school, I was _obsessed_ with losing my virginity,” Stiles continues, still fiddling with his coffee cup. “Seriously, I talked about it so freaking much. And then I actually had sex for the first time and it was _horrible_ , because I didn’t want to admit to the guy that I was a virgin and I had been drinking because I was nervous and _he_ been drinking, too…” Stiles sighs. “Basically it was just a disaster.”

This is the perfect opportunity to tell him, Derek thinks. It’s the perfect time to admit that he hasn’t actually had sex yet and that he’s been telling white lies these past few months all as an excuse to talk to Stiles. But, well, will Stiles think he’s part of the problem then? Will he think that Derek’s ashamed of his lack of sexual experience? 

Because he isn’t, not really. He could have had sex a thousand times already if he wanted to, but he _hasn’t_ wanted to. Really, the only person he’s ever wanted enough to make an effort for is Stiles –

Huh. He’s never really thought of it in those terms before.

“That didn’t completely turn you off from sex?” Derek asks instead, chickening out from admitting everything to Stiles, deciding to keep the conversation focused on him.

“It did for a little while,” Stiles says, shrugging. “But then I complained about it to a friend and she practically beat me over the head for being an idiot about my approach to sex.”

“Well, it _was_ pretty stupid,” Derek snorts, smirking slightly and making Stiles swat at him playfully.

“Watch it, Dental Dam Derek,” Stiles shoots back, using the nickname he knows Derek hates. Really, now it’s just reserved for when Stiles is annoyed with him. (Erica continues to use it every time she sees him, though, much to his embarrassment and frustration.)

Their conversation continues on like that, but it steadily moves to more casual, comfortable topics. Derek can’t help but feel inordinately pleased as he watches the way the tension slowly bleeds out of Stiles’ shoulders and the way his eyes start to light up again, mouth curling into a gentle smile.

He’s not sure how long they talk for – a few hours at least. But soon enough, Stiles’ shift is done and Derek needs to get back home to finish an essay.

Well, finish an essay and look up a few things online.

\---

Derek has an entire speech prepared when he goes to talk to Stiles the next day. It includes phrases like “bisexual, but gray-asexual” and “hot like burning.” Really, he kept trying to cut out the “hot like burning” part, but it kept popping up in other sections. He pretty much given up on denying it now.

However, as soon as he walks through the doors of the Student Sexual Health Center, he freezes.

Because right there, standing at the front desk talking to Stiles, is Laura. Fuck.

“Seriously, he’s totally your type,” Laura says, her back turned to him as she leans over the desk. “Just one date. In fact, it doesn’t even have to be a date.”

“Laura,” Stiles whines, as Derek just stands there, frozen. “I’m not really looking – ”

The door slams shut behind him. Loudly.

“Oh, hey – if it isn’t my awkward virgin brother now!” Laura announces, beaming brightly at him. Thankfully the lobby is empty except for the three of them. “I was just telling Stiles that maybe you could use some of his experience.”

Derek’s not paying attention to her, though, instead staring at Stiles like a deer caught in the headlights of an oncoming car. Stiles stares back at him for a moment, wide eyed.

Then, he starts laughing.

“Oh my god, Laura, he’s really – ” Stiles has to pause for a moment as his body shakes with giggles. “There’s _no way_ Derek’s a virgin.”

“Stiles, shut up,” Derek snaps, striding up to the desk, his face turning bright, bright red.

“Wait, you mean – ” Stiles asks, the grin disappearing from his face.

“Laura, I fucking told you to keep your nose out of this!” Derek growls, ignoring Stiles, still flushed in shame.

“Derek, I swear I didn’t know,” Laura replies, looking between him and Stiles, a pained look on her face. “If I’d known, I – ”

“Can we talk in private?” Derek asks, interrupting her and turning to Stiles, directing the question at him.

“Yeah, sure,” Stiles says, biting his lip and standing up from his desk. “We can use one of the exam rooms.”

Derek nods stiffly and follows him, shooting his sister a glare over his shoulder, trying not to let his anger dissipate any at the guilty look on her face. It’s obvious that she really didn’t know that Stiles was who he’d been crushing on for the past few months, but _still_.

“So,” Stiles says awkwardly after Derek closes the door behind him. “I, uh, I’m super sorry for laughing at you. I wasn’t trying to – I just – with the questions you kept asking, I thought – ”

“It’s not your fault,” Derek sighs, scrubbing a hand over his face, grateful that his blush seems to have gone down at least a little bit. “I was the one who lied to you.”

“No you didn’t,” Stiles protests, a frown on his face. “You just asked questions and I assumed – ”

“I led you on. I was trying to make you assume what you did,” Derek replies, crossing his arms over his chest, eyes fixed on a spot on the wall behind Stiles’ head, carefully not making eye contact.

“I wouldn’t have judged you,” Stiles says softly, and Derek _knows_ that – he really does. He feels so, so guilty about making Stiles feel like this is somehow his fault.

“I know you wouldn’t have,” Derek sighs, adjusting his glasses awkwardly. “I just – I needed an excuse to talk to you, and sex questions seemed like the best option.”

It sounds so incredibly lame and pathetic now that he’s said it out loud.

“You needed an excuse to talk to me?” Stiles repeats, his brow furrowing in confusion, but there’s a note of something that might be _hope_ in his tone.

“I got a B- in Modern Asian Lit, because I spent the whole class paying attention to you instead of the prof,” Derek admits, cheeks flushing again, still not meeting Stiles’ eyes.

The room’s silent for a moment and Derek tentatively looks up to find Stiles staring at him with wide eyes, his distracting mouth hanging open in shock.

“Look, I hope this won’t make things weird between us – ” Derek starts, his heart sinking in his chest, but Stiles cuts him off.

“No! It’ won’t – I just – ” Stiles stutters, cheeks turning pink. “I got a C in that class, because I kept daydreaming about you.”

“What?” Derek replies, because he _must_ have heard wrong.

“You’re the hot guy I mentioned,” Stiles mumbles, looking over at Derek from under his long eyelashes. “I just didn’t think you were into me like that.”

“I’ve never been attracted to someone like I’m attracted to you before,” Derek admits tentatively, slowly, uncrossing his arms and clenching his hands into fists by his sides. “I wasn’t lying about being bisexual, but I think I’m also gray-asexual.”

“Then we’ll take things slowly,” Stiles replies, smiling slightly. “Or, you know, at whatever pace you want.”

“I, um,” Derek stutters, cheeks still a little flushed as he looks over at Stiles. “I was thinking maybe we could start with dinner sometime.”

“My shift ends in an hour,” Stiles says, eyes bright.

Derek smiles.

\---

“You sure you’re ready for this?” Stiles gasps as he breaks the kiss, lips swollen and pupils dilated attractively.

“ _Yes_ , Stiles, for the last time,” Derek growls, pressing Stiles back against the wall and grinding up against him to demonstrate just how ready he is.

“And remember that you can change your mind at any time – ” Stiles says, but Derek cuts him off, swooping in for another kiss, delving into Stiles’ mouth with his tongue and enjoying the way Stiles moans against his lips.

“Fuck,” Stiles gasps as they break apart again, still clutching Derek’s shirt tightly. “You are the bossiest virgin I’ve ever met.”

“Not for long,” Derek replies, smirking and leaning down to kiss at Stiles’ neck experimentally, getting more and more confident as Stiles shivers and bucks his hips.

“Bed, _now_ ,” Stiles demands, pushing off the wall and tugging on Derek’s shirt, dragging him the few feet over to his bed.

“Top or bottom?” Derek asks, taking his shirt off maybe a little too quickly and nearly getting caught in it.

“Hey, don’t get ahead of yourself,” Stiles laughs, helping Derek out of his shirt. “I was thinking I could just blow you for now, if that’s okay?”

“ _Only_ a blowjob, I’m so disappointed, Stiles,” Derek deadpans, his tone teasing, and Stiles pushes him back onto the bed in retaliation.

But then, well, then Derek’s swallowing any smart remarks he might still have in him, because Stiles is on top of him, shoving his jeans and underwear down around his thighs and producing a condom from his pocket. Derek groans as Stiles opens it and quickly rolls it down his cock, his movements efficient and practiced.

“Don’t worry about fucking my mouth, okay?” Stiles says, settling between Derek’s thighs and looking over at him, licking his already saliva-slick lips. “I have, like, no gag reflex anymore. And feel free to pull my hair, too.”

“Yeah,” Derek breathes, carding his fingers through Stiles’ messy hair, enjoying the way Stiles leans into his touch. “Yeah, okay.”

Stiles grins and then ducks his head down, licking a long stripe along the underside of Derek’s cock. His grip on Stiles’ hair tightens a little as Stiles takes the head of his cock into his mouth, sucking on it for a while before sliding down and taking in more. Derek can’t help but buck his hips up off the bed, thrusting a little deeper into Stiles’ mouth, but Stiles takes it all in stride, hardly even faltering.

“Fuck,” Derek gasps, mesmerized by the look on Stiles face, the way he hollows his cheeks and the way his swollen lips are wrapped around his cock.

Derek knows he’s not going to last long, not when it’s his first time and someone as talented as Stiles is going down on him. He tugs on Stiles’ hair tentatively, drawing him in a little closer, until Stiles’ nose is brushing up against dark hair. Stiles looks up at him through long eyelashes, a heated spark in his eyes, before drawing back just a little bit and tugging at Derek’s hips, encouraging him to fuck up into his mouth.

Derek hesitates for a moment, still wary of choking Stiles, but then Stiles’ eyes flutter shut and he _moans_ , making Derek swear as he feels the vibrations. He complies, then – thrusting up into the wet heat of Stiles mouth three, four, five times before he’s gasping and shuddering, emptying himself into the condom.

“Good?” Stiles asks after pulling off Derek’s softening cock, his voice a little hoarse.

“Fuck yes,” Derek pants, pulling Stiles up and into another kiss.

It’s demanding this time, more so than before, at least. Stiles pries his mouth open roughly with his tongue, delving inside. The slick slide of their lips together is almost bruising, and there’s the occasional clash of teeth due to Derek’s lack of finesse, but it’s so, so good. Derek can feel the rigid outline of Stiles cock pressing up against his hip, still confined by Stiles’ jeans. 

With fumbling hands – trying not to break the kiss – Derek reaches down to unbutton and unzip Stiles’ pants, but it takes him a few tries, and he finds himself swearing against Stiles’ lips, frustrated and overeager. Stiles lets out a little laugh and pulls back, Derek letting out a frustrated huff at the action.

“Lube?” Stiles pants, making quick work of his jeans and boxers, groaning as he finally frees his cock.

“I have – ” Derek says, twisting around and stretching to reach the top drawer of his bedside table, wrenching it open. “It should be – ”

His hand wraps around the bottle and he pulls it out. He squirts what’s probably too much onto his hand, but he’s too sexed up and eager to really care.

“Hey!” Stiles squawks, tipping forward a little as Derek wraps a hand around his cock, jacking him experimentally. “That’s cold!”

“Sorry,” Derek apologizes, faltering, his cheeks flushing red as Stiles points out his mistake. “Sorry, I – ”

“Oh no, don’t you dare stop,” Stiles demands, moaning as he thrusts forward into Derek’s hand. “If you stop now I will literally kill you.”

“Who would get you off then?” Derek retorts, stroking Stiles at a torturously slow pace, wanting to see him flushed and desperate, but also getting used to the feel of someone else’s cock in his hand. It’s strange, with the unfamiliar curve and slightly different thickness of Stiles’ cock, but it’s certainly not bad.

“Fuck,” Stiles gasps, cheeks red and mouth hanging open as he pants. “Fuck, _Derek_ – ”

Derek grows a little more confident then, squeezing a little tighter, moving a little faster. Stiles moves his hips a little, too, easily matching Derek’s rhythm. The slick sound of lube against skin reverberates through the room along with heavy breathing and Stiles’ shameless moans. But then Derek feels Stiles falter slightly and a moment later, he’s coming.

Derek jacks him through his orgasm until Stiles whines slightly and bats his hand away, overstimulated. Stiles slumps forward against his chest, against the still wet come painting his stomach and hand.

“So, as far as first times go, how do you think that went?” Stiles asks once he’s caught his breath again, the words murmured against the side of Derek’s neck.

“Two out of five stars,” Derek says, shrugging, which earns him a glare and a kick from Stiles. “I’m kidding! I’m kidding!”

“You better be!” Stiles retorts, looking mildly affronted, scowling at him.

“It was amazing, okay?” Derek replies, wrapping an arm around Stiles and holding him close, pressing a kiss to his temple. “I think I still have some room for improvement, though.”

“Yeah, I suppose you never actually took your Anal 101 exam,” Stiles says, grinning at him suggestively.

Derek laughs and kisses him again.

**Author's Note:**

> Please note that I'm a cis female who mostly has sexual experience with sex with other cis women. I have some experience with cis men, too, but like I said, I'm not a gay man and therefore have never had gay male sex. So sorry for any inaccuracies.
> 
> _I do not give permission to have any of my works put up on goodreads or any other such site._


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